Isolation of indolmycin and its derivative as antagonists of L-tryptophan.

Hirota, Akira; Higashinaka, Yuji; Sakai, Heiichi

doi:10.1271/bbb1961.42.147

Cited by 5 publications

(4 citation statements)

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“…Molecules bearing 2-oxazoline rings display diverse biological activities including antibiotic, anti-inflammatory, antimalarial, anticancer, and antidepressant actions. In addition, the 2-oxazoline function has already proved its synthetic utility as a carboxylic acid protecting group and ligand in asymmetric synthesis, − being pyridino-bis-2-oxazolines (PYBOX) and bis-oxazolines (BOX) the most frequently used derivatives.…”

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Regioselective Functionalization of Ester-, Amide-, Carbonate-, and Carbamate-Substituted 2-Phenyl-2-oxazolines with Mixed Lithium–Magnesium Amides

et al. 2020

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We have prepared novel highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium−magnesium amides followed by reaction with different electrophiles. While a complementary metalation site can be accessed by using different bases, steric and electronic effects promoted by the aromatic ring substituents also play an important role in reaction regioselectivity. Computational calculations of the aromatic hydrogen pK a values have helped us to rationalize the metalation preference by the complex-induced proximity effect concept.

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confidence: 99%

Regioselective Functionalization of Ester-, Amide-, Carbonate-, and Carbamate-Substituted 2-Phenyl-2-oxazolines with Mixed Lithium–Magnesium Amides

et al. 2020

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“…The compound is active against grampositive and gram-negative bacteria and Mycobacterium tuberculosis (PADE-ISKAYA et al, 1972). It was recently isolated again from S. griseus, together with N-demethyl-C-demethylindolmycin (2) as an active agent in a screen for L-tryptophan antagonists in E. coli (HIROTA et al, 1978). Consistent with this antimetabolite activity, mode of action studies have shown (WERNER et al, 1976) that indolmycin prevents formation of tryptophanyl-tRNA in prokaryotes, but not eukaryotic cells, by inhibiting, competitively with tryptophan, the prokaryotic tryptophanyl-tRNA ligase.…”

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confidence: 98%

Biosynthesis

1981

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“…Indolmycin(IM) was prepared according to the method reported by Hirota et al 3 ) Streptomyces griceus No. 927 was cultured at 30°C for two days in bouillon medium.…”

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confidence: 99%